CN105636457B

CN105636457B - Organic compounds with taste-improving properties

Info

Publication number: CN105636457B
Application number: CN201380080022.7A
Authority: CN
Inventors: A·德克勒克; H·雷尼斯; C·温克尔
Original assignee: Givaudan SA
Current assignee: Givaudan SA
Priority date: 2013-10-02
Filing date: 2013-10-02
Publication date: 2020-03-10
Anticipated expiration: 2033-10-02
Also published as: EP3057445A1; EP3057445B1; US20160242444A1; CN105636457A; US10834943B2; WO2015048990A1

Abstract

The present disclosure relates to flavour modification and compounds of formula (I) wherein R is¹Is selected from C₆‑C₂₀Alkyl and C₉‑C₂₅Alkenyl radical, R⁵Is C₁‑C₃Alkyl, and a) n is 1; and i) R³And R⁴Is hydrogen, and R²Is a proteinogenic amino acid residue; ii) R²And R³Is methyl, and R⁴Is hydrogen; or R⁴Is hydrogen and R²And R³Together with the carbon atom to which they are attached form a cyclopropyl group; iii) R²Is hydrogen, and R³And R⁴Together are-CH₂‑CH₂‑CH₂-; b) n is 2 or 3, and R²、R³And R⁴Is hydrogen.

Description

Organic compounds with taste-improving properties

The present disclosure relates to flavour modification and compounds for modifying flavour.

The addition of flavour to edible products, i.e. products that are ingested orally (e.g. foods, confectionery and beverages) or spit out (e.g. toothpaste and mouthwashes) is a long established practice. The fragrance can be modified by the addition of other fragrance ingredients, which is generally within the purview of the ordinary perfumer.

More recently, it has been desired to improve the aroma by adding materials which are not standard aroma ingredients themselves, i.e. they do not have the desired taste (if any) suitable as aroma ingredients, but can improve the aroma in a certain desired way when used in very low concentrations. Some examples of these include:

-a flavour enhancer. They enhance the fragrance or some aspect of the fragrance. For example, sweetness enhancers may be added to edible products to provide the same level of sweetness at a reduced sugar content. Enhanced salty taste is another category of such enhancements. This has become of paramount importance in the production of health and dietary food, where reduced levels of salt and/or sugar are desired.

-an off-flavour masking agent. It is well known that some desirable flavour ingredients suffer from the disadvantage of also providing an undesirable off-flavour. One example is the "metallic" off-taste sometimes associated with some high intensity sweeteners. Masking agents can block these off-tastes and enable the fully desired flavour impact to be achieved without drawbacks.

-mouthfeel enhancers. Although not strictly aroma-like, mouthfeel can be significantly added or subtracted from the edible composition. Undesirable mouthfeel can be a serious drawback for otherwise desirable flavour compositions.

Another desire in the industry is to more completely generate flavors that capture natural, authentic flavors in high volume edible compositions, particularly foods and beverages. For example, it is often desirable to develop an orange flavored beverage taste as close as possible to freshly squeezed orange juice. It is generally known that during the preparation of commercial orange flavored beverages, more of the true orange flavor is inevitably lost. This is true in a variety of mass-produced foods and beverages.

It has now been found that the addition of certain compounds to an edible composition comprising a flavour may desirably improve the flavour therein in one or more of the ways mentioned above, resulting in a composition that is more appealing to the consumer. Thus, there is provided a method of improving the taste of an edible composition comprising at least one flavour co-ingredient, the method comprising incorporating therein a flavour modifying proportion of a compound of formula (I),

wherein

R¹Is selected from C₆-C₂₀Alkyl and C₉-C₂₅An alkenyl group, which is a radical of an alkenyl group,

R⁵is C₁-C₃Alkyl, such as ethyl, propyl or isopropyl, and

a) n is 1; and is

i)R³And R⁴Is hydrogen, and R²Is a proteinogenic amino acid residue;

ii)R²and R³Is methyl, and R⁴Is hydrogen; or R⁴Is hydrogen, and R²And R³Together with the carbon atom to which they are attached form a cyclopropyl group;

iii)R²is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-；

b) n is 2 or 3, and R²、R³And R⁴Is hydrogen.

Proteinogenic amino acids having the general structure of formula (II)

Selected from alanine (Ala; R)²Methyl), cysteine (Cys; r²＝CH₂-SH), aspartic acid (Asp; r²＝CH₂-C(O)O^-) Phenylalanine (Phe; r²＝CH₂-phenyl), glutamic acid (Glu; r²＝CH₂-CH₂-C(O)O^-) Histidine (His; r²＝CH₂-imidazole), isoleucine (IIe; r²2-methyl-but-2-yl), lysine (Lys; r²＝(CH₂)₄NH₃ ⁺) Leucine (Leu; r²Isobutyl), methionine (Met; r²＝(CH₂)₂-S-CH₃) Asparagine (Asn; r²＝CH₂C(O)NH₂) Glutamine (Gln; r²＝(CH₂)₂C(O)NH₂) Arginine (Arg; r²＝(CH₂)₃NHC(NH₂)⁺NH₂) Serine (Ser; r²＝CH₂OH), threonine (Thr; r²＝CH(OH)CH₃) Valine (Val; r²Isopropyl), tryptophan (Trp; r²CH 2-1H-indole), tyrosine (Tyr; r²＝CH₂-phenol) and glycine (Gly; r²＝H)。

Reference herein to "alkyl" of a compound of formula (I) means straight and branched chain C unless otherwise indicated₆-C₂₀Alkyl, preferably C₁₂-C₂₀E.g. C₁₆、C₁₈An alkyl group;

"alkenyl" means straight and branched chain C₉-C₂₅Alkenyl radicals including C₁₀、C₁₁、C₁₂、C₁₃、C₁₄、C₁₅、C₁₆、C₁₇、C₁₈、C₁₉、C₂₀、C₂₁、C₂₂、C₂₃And C₂₄Alkenyl groups comprising 1-6 (e.g., 2, 3, 4, or 5 double bonds).

In one embodiment, R¹Together with the carbonyl group to which it is attached, is a carboxylic acid residue containing 8 to 22 carbon atoms.

In another embodiment, R¹Together with the carbonyl group to which it is attached, is a fatty acid (R)¹COOH) residues, e.g. R¹Is C₈-C₂₂A fatty acid residue. The fatty acid may be a mammalian or non-mammalian fatty acid. Mammalian fatty acids are natural or synthetic fatty acids that are structurally identical to one that occurs naturally in mammals, including, but not limited to, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, arachidonic acid, eicosapentaenoic acid (eicosapentaneoic acid), and docosatetraenoic acid. Non-mammalian fatty acids are natural or synthetic fatty acids not normally produced by mammals, including, but not limited to, pentadecanoic acid; heptadecanoic acid; nonadecanoic acid; heneicosanoic acid; 9-trans-decatetraenoic acid; 10-transPentadecenoic acid of the formula; 9-trans-hexadecenoic acid; 10-trans-heptadecenoic acid; 10-trans-heptadecenoic acid; 7-trans-nonadecenoic acid; 10, 13-nonadecadienoic acid; 11-trans-eicosenoic acid; and 12-trans-eicosenoic acid.

The fatty acid residues may be saturated or unsaturated. If they are unsaturated, they preferably have 1, 2 or 3 double bonds, which may be in the cis-or trans-configuration.

A non-limiting example is a compound of formula (I), wherein R⁵Is methyl.

A further non-limiting example is a compound of formula (I) wherein R¹Is a fatty acid residue, e.g. selected from C₁₆-C₁₈A fatty acid residue, which may be saturated or unsaturated.

A further non-limiting example is a compound of formula (I) wherein R³Is hydrogen.

A further non-limiting example is a compound of formula (I) wherein R³Is hydrogen, R²Is an α amino residue of protein origin, and R¹Is an unsaturated fatty acid residue containing 2, 3 or 4 double bonds.

A further non-limiting example is a compound of formula (I) wherein R¹Is a residue of an unsaturated fatty acid selected from the group consisting of myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, arachidonic acid, eicosapentaenoic acid and docosatetraenoic acid, geranic acid (3, 7-dimethyl-2, 6-octadienoic acid).

Further non-limiting examples are compounds of formula (I) selected from the group consisting of (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate; (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate; (E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate; (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -3- (1H-imidazol-4-yl) propionate; 1- ((9Z,12Z) -octadeca-9, 12-dienoyl) pyrrolidine-2-carboxylic acid methyl ester; 4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester and 2- ((9Z,12Z,15Z) -octadeca-9, 12, 15-trienamido) propanoic acid methyl ester.

The compounds of formula (I) may be prepared according to methods well known in the art using commercially available starting materials, reagents and solvents. For example, the compounds of formula (I) may be prepared by reacting the corresponding amino acid alkyl ester with the corresponding fatty acid. The fatty acid may be used as a free fatty acid in combination with a coupling (dehydration) reagent or as an activated fatty acid, such as a fatty acid chloride.

The compounds of formula (I) as described above impart a remarkable organoleptic profile to the edible products to which they are added. In particular, they deliver a highly intense, realistic and coordinated aroma and rounding and fullness to the edible products containing them.

A more surprising aspect of this finding is the consideration that when applicants taste compounds in the form of dilute aqueous solutions, they exhibit disappointing, weak fatty taste characteristics. As such, they are clearly quite unsuitable for use in fragrance applications. Only their combination with flavor co-ingredients and a very heavy choice of the level of their use enable to find the remarkable organoleptic properties of these compounds. A very rare aspect of their effect on edible products is that they actually complement, enhance or enhance the basic or true flavor and mouthfeel characteristics of the food or beverage into which they are incorporated. Thus, the compounds of the present invention find application in a wide range of products in the food and beverage industry as well as in health and wellness.

Thus, in another aspect, there is provided a method of imparting flavour and/or mouthfeel, or improving the taste and/or mouthfeel, of an edible composition, which method comprises adding to said composition a compound of formula (I) as defined herein.

When the compounds of formula (I) are incorporated into an edible composition comprising one or more flavour co-ingredients, a significant organoleptic effect is observed.

Thus, in another embodiment, an edible composition is provided comprising an edible composition base, at least one flavour co-ingredient and a flavour-modifying proportion of a compound of formula (I) as defined herein.

By "flavour co-ingredient" is meant an ingredient capable of contributing or imparting or modifying a taste to an edible composition in a positive or pleasant way, such as sugars, fats, salts (e.g. sodium chloride), MSG (monosodium glutamate), calcium ions, phosphate ions, organic acids, proteins, purines, flavours and mixtures thereof. The flavour co-ingredients may also include salty tastants, umami tastants and flavoured flavour compounds.

By "taste" is meant those sensations felt through the oral cavity, including salty, sweet, sour, bitter, and umami.

Non-limiting examples of flavor adjunct ingredients include: NaCl, KCl, MSG, Guanosine Monophosphate (GMP), Inosine Monophosphate (IMP), ribonucleotides such as disodium inosinate, disodium guanylate, N- (2-hydroxyethyl) -lactamide, N-lactoyl-GMP, N-lactoyl tyramine, gamma aminobutyric acid, allylcysteine, 1- (2-hydroxy-4-methoxyphenyl) -3- (pyridin-2-yl) propan-1-one, arginine, potassium chloride, ammonium chloride, succinic acid, N- (2-methoxy-4-methylbenzyl) -N' - (2- (pyridin-2-yl) ethyl) oxamide, N- (hept-4-yl) benzo (D) (1,3) dioxole-5-carboxamide, n- (2, 4-dimethoxybenzyl) -N '- (2- (pyridin-2-yl) ethyl) oxamide, N- (2-methoxy-4-methylbenzyl) -N' -2(2- (5-methylpyridin-2-yl) ethyl) oxamide, cyclopropyl-E, Z-2, 6-nonadienamide.

In a particular embodiment, the saccharide is present in an amount of 0.001% to 90%, more particularly 0.001% to 50%, still more particularly 0.001% to 20% by weight of the total edible composition.

For example, sugars (e.g., sweeteners such as sucrose, high fructose corn syrup, fructose, and glucose; high intensity non-nutritive sweeteners such as aspartame, acesulfame potassium, sucralose, cyclamates, saccharin Na +, neotame, rebaudioside A, and/or other stevia-based sweeteners) may constitute up to 20% of the total weight of the comestible composition in the beverage.

Examples of sweetener concentrations typically present in beverages are:

carbonated soft drinks: < 1% -15% sweetener; non-carbonated beverage (no alcohol): < 1% -15% sweetener; a fruit juice beverage; < 1% -15% sweetener; powder soft drink: < 1% -20% sweetener; liquid concentrate: < 1% -20% sweetener; alcoholic beverages: < 1% -40% sweetener; functional beverage: < 1% -20% sweetener; coffee-based beverages: < 1% -15% sweetener; and tea-based beverages: < 1% -15% sweetener.

In a particular embodiment, the fat is present in an amount of 0.001% to 100%, more particularly 0.001% to 80%, more particularly 0.001% to 30%, still more particularly 0.001% to 5% by weight of the total weight of the edible composition.

In a particular embodiment, the salt (e.g., sodium chloride) is present in an amount of 0.001% to 20%, more particularly 0.001% to 5%, by weight of the total edible composition.

In a particular embodiment, MSG is present in an amount of 0.001% to 2% by weight of the total edible composition.

In a particular embodiment, calcium is present in an amount of 0.001% to 50%, more particularly 0.001% to 20%, still more particularly 0.001% to 1% by weight of the total edible composition.

In a particular embodiment, the organic acid is present in an amount of 0.001% to 10%, more particularly 0.001% to 7% by weight of the total edible composition. Types of organic acids include citric acid, malic acid, tartaric acid, fumaric acid, lactic acid, acetic acid, and succinic acid. Types of edible products comprising organic acids include beverages, such as carbonated soft drinks, still drinks, juices, powdered soft drinks, liquid concentrates, alcoholic beverages, and functional beverages.

In a particular embodiment, the phosphorus is present in an amount up to 0.5% by weight of the edible composition. Typically, phosphorus is present as a phosphate or phosphoric acid.

In a particular embodiment, the purines are present in an amount up to 0.5% by weight of the edible composition. The term "purines" includes ribonucleotides such as IMP and GMP.

In a particular embodiment, the flavour is present in an amount of up to 15% by weight of the edible composition, for example in an amount of 0.01 to 15% by weight (e.g. 10 to 15% by weight in snacks, 0.1 to 0.5% by weight in flavoured foods, 0.01 to 0.1% by weight in sweets and dairy products).

All forms of flavors may be used in the compositions of the present invention including, but not limited to, natural flavors, artificial flavors, spice flavorings, condiments, and the like. Fragrances include synthetic and perfuming fragrances and/or oils, oleoresins derived from plants, leaves, flowers, fruits and the like, essential oils, distillates and extracts, and combinations comprising at least one of the foregoing ingredients.

The scented oil comprises spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, nutmeg oil, allspice, sage oil, nutmeg, bitter almond oil, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla and citrus oil, including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, prune, raisin, cola, guarana, orange blossom oil, pineapple, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya, and the like.

Additional exemplary flavors delivered by the flavor composition include milk flavors, butter flavors, cheese flavors, cream flavors, and yogurt flavors; vanilla flavor; tea or coffee essences such as green tea essence, oolong tea essence, cocoa essence, chocolate essence and coffee essence; mint flavors such as peppermint, spearmint and japanese mint; spicy essences such as asafetida essence, celery essence, anise essence, swertia essence, fennel essence, allspice essence, cinnamon essence, chamomile essence, mustard essence, cardamom essence, caraway essence, fennel fruit essence, clove essence, pepper essence, coriander fruit essence, sassafras essence, celery essence, zanthoxylum essence, perilla essence, juniper berry essence, ginger essence, anise essence, horseradish essence, thyme essence, wormwood essence, dill seed essence, capsicum essence, nutmeg essence, basil essence, marjoram essence, rosemary essence, bay leaf essence, and green mustard (japanese horseradish) essence; nut essences such as almond essence, hazelnut essence, nut essence, peanut essence, pecan essence, pistachio essence, and walnut essence; alcoholic flavors such as wine flavor, whisky flavor, brandy flavor, liqueur flavor, gin flavor and liqueur flavor; a floral essence; and vegetable flavors such as onion flavor, garlic flavor, cabbage flavor, carrot flavor, celery flavor, lentinus edodes flavor and tomato flavor.

In some embodiments, the flavor compositions include aldehydes and esters, such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarvacrol acetate, eugenol 49 formate, p-methyl anisic alcohol (amisol), and the like, may be used additional examples of aldehyde flavors include acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, anise), cinnamaldehyde (cinnamon), citral, i.e., α -citral (lemon, lime), neral, i.e., β -citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotropine, i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), α -amyl cinnamic aldehyde (spicy fruit essence), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifier, many types), decanal (citrus fruit), aldehyde C-8 (citrus fruit), citral C-9 (citrus fruit), citrus fruit aldehyde C-12 (citrus berry), 2-ethyl cinnamaldehyde (geranial), cinnamic aldehyde (2-6-dimethyl cinnamaldehyde (cucurbital), 2-6-hexenal (cucurbital), cucurbital, 2-6-methyl cinnamaldehyde, 2-6-hexenal (cucurbital), and the like, may be used.

Further examples of other fragrances can be found in "used in Food Processing" by National Academy of Sciences, volume 1274, pages 63-258.

In preparing the edible composition, the compound of formula (I) may be used in any physical form. They can be used in neat form, in stock solutions; they may be used in the form of an emulsion; or they may be used in powder form. If the compound of formula (I) is present in powder form, the powder form can be produced by a dispersion evaporation process, for example a spray drying process. The liquid preparation may comprise a solution, suspension or emulsion comprising a compound of formula (I). The liquid product may comprise further ingredients, such as carrier materials and/or adjuvants suitable for fragrance compositions.

In another embodiment, the compound of formula (I) may be mixed with flavor adjuvants, in particular with flavors, and then incorporated into the edible composition base.

Thus, in another aspect, there is provided a fragrance composition comprising a compound of formula (I) as defined herein and at least one fragrance adjunct ingredient, in particular a perfume, and optionally a carrier material and/or an adjunct suitable for the fragrance composition.

The carrier material may be used to encapsulate or entrap a compound of formula (I) or a composition comprising a compound of formula (I), in particular a fragrance composition, in a matrix. The carrier material may function solely as a processing aid or filler, or may serve to shield or protect other ingredients from moisture or oxygen or any other aggressive media. The carrier material may also function as an article to control the release of flavor from the edible product when consumed.

The carrier material may comprise mono-, di-or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins. Examples of specific carrier materials include sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt (isomalt), sorbitol, mannitol, xylitol, lactitol, maltitol, pentitol (pentatol), arabinose, pentose, xylose, galactose, maltodextrin, dextrin, chemically modified starch, hydrogenated starch hydrolysate, succinylated or hydrolyzed starch, agar, carrageenan, gum arabic, acacia gum, tragacanth gum, alginate, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, derivatives and mixtures thereof. Of course, it will be understood by those skilled in the art that the materials referred to are incorporated herein by way of example and are not to be construed as limiting the invention.

By "fragrance aid" is meant an ingredient that is capable of imparting additional added benefits to the compositions of the present invention, such as color, light fastness, chemical stabilizers, and the like. Suitable adjuvants include solvents (including water, alcohols, ethanol, triacetin, oils, fats, vegetable oils, and miglyol), binders, diluents, disintegrants, lubricants, colorants, preservatives, antioxidants, emulsifiers, stabilizers, anti-caking agents, and the like. In a particular embodiment, the flavour composition comprises an antioxidant. The antioxidant may include vitamin C, vitamin E, rosemary extract, t-butyl-p-cresol, Butylated Hydroxyanisole (BHA), and Butylated Hydroxytoluene (BHT).

Examples of such carrier Materials or adjuvants for fragrance compositions may be found in, for example, "Perfume and flavour Materials of Natural Origin", s.arctander, ed, Elizabeth, n.j., 1960; "Perfuel and Flavour Chemicals", S.arctander, Ed., Vol.I & II, Allured publishing corporation, Carol Stream, USA, 1994; "Flavourings", E.Ziegler and H.Ziegler (ed.), Wiley-VCH Weinheim, 1998 and "CTFA Cosmetic Ingredient Handbook", J.M.Nikitakis (ed.), 1 st edition, The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

Other suitable and desirable ingredients of the fragrance composition are described in standard textbooks such as "Handbook of industrial Chemical Additives", ed.m. and i.ash, 2 nd edition (Synapse 2000).

The flavour composition of the present invention may be provided in any suitable physical form. For example, they may be in the form of an oil, emulsion or dispersion in an aqueous or organic liquid suitable for use in edible products or in solid form, such as a powder.

If the flavour compositions are provided in the form of powder compositions, they may be prepared by dispersion evaporation techniques generally known in the art, such as spray drying.

Thus, in another embodiment of the present invention, there is provided a method of forming a powder composition, the method comprising the steps of: providing a liquid composition comprising a compound of formula (I) and one or more optional ingredients selected from at least one flavour co-ingredient, a carrier material and an adjunct; and dispersively evaporating the liquid composition to form a powder composition.

In this way, the compound of formula (I) or the flavour composition comprising said compound may be made in powder form.

The liquid composition used to prepare the powder may be in the form of a solution, emulsion, dispersion or slurry. The liquid may comprise water and/or an organic liquid, such as ethanol, glycerol, triacetin, miglyol (mct) acceptable for use in edible products.

The powder composition of the present invention can be prepared according to methods and apparatuses used in the art for the industrial scale production of powders. A particularly suitable method is spray drying. Spray drying techniques and equipment are well known in the art and need not be discussed in detail herein. The spray drying techniques, apparatus and methods described in US2005/0031769 and US2013/0022728 and those described in those references are suitable for producing powder compositions and are incorporated herein by reference in their entirety.

As mentioned above, compounds of formula (I) or flavour compositions comprising such compounds may be incorporated into edible products, and edible compositions or flavour compositions comprising such compounds of formula (I) constitute further aspects of the invention.

The term "edible composition" refers to a product that is consumed by a subject, typically through the oral cavity (although consumption may be by non-oral means, e.g., inhalation), for at least one purpose of enjoying, nutritional, or health and wellness benefits. The edible product may be in any form including, but not limited to, liquid, solid, semi-solid, tablet, capsule, lozenge, stick, powder, gel, gum, paste, slurry, syrup, aerosol, and spray. The term also refers to, for example, dietary and nutritional supplements. Edible products include compositions that are placed in the oral cavity for a period of time before being discarded without swallowing. It may be placed in the mouth prior to consumption, or it may be left in the mouth for a period of time and then discarded. Edible compositions as defined above include compositions whose taste is altered by the addition of a compound of formula (I) in the manner described herein.

Broadly, edible compositions include, but are not limited to, all kinds of food products, confectionery products, baked goods, desserts, flavored products, fermented products, dairy products, beverages, and oral care products.

In a particular embodiment, the term "edible product" refers to a product that is consumed by a subject, typically through the oral cavity (although consumption may be by non-oral means such as inhalation), for one of the purposes of enjoyment or nutrition.

In a more specific embodiment, the term "edible product" refers to a product intended for enjoyment by a subject, typically by oral consumption (although consumption may be by non-oral means such as inhalation). More specifically, the term refers to food and beverages.

Exemplary food products include, but are not limited to, quick frozen snacks, sweet and excellent flavored snacks, fruit snacks, fried potato chips/chips, puffed snack foods, tortillas/corn chips, popcorn, pretzels, nuts, other sweet and excellent flavored snacks, low fat cookies, breakfast bars, energy bars, fruit bars, other snacks, meal replacers, weight loss products, refreshment beverages, ready-to-eat meals, canned ready-to-eat meals, frozen ready-to-eat foods, dried meals, frozen ready-to-eat meals, mixed snacks, quick frozen pizzas, soups, canned soups, soup powders, instant soup powders, cold soups, super-warm soups, frozen soups, pasta, canned pasta, dry pasta, frozen/fresh pasta, noodles, sun-spring noodles, instant noodles, cupped/bowl-packed instant noodles, bagged instant noodles, oil-vinegar noodles, instant noodles, snack foods, instant noodles, dried foods, assorted snacks, soy sauce, seasonings and seasonings, herbal and spice seasonings, pasty foods, jams and preserves, honey, chocolate paste, nut-based paste and fermented flour paste.

Exemplary confectionery products include, but are not limited to, chewing gums (including sugared chewing gums, sugarless chewing gums, functional chewing gums and bubble gums), center-filled confections, chocolate and other chocolate confections, medicated confections, brittle hard candies, tablets, soft fruit cakes, mints, standard mints, hard mints, soft candies, hard candies, breath and other oral care films or strips, candy sticks, lollipops, gummies, jellies, fudge, caramel, hard and brittle loose candies, toffee, taffy, licorice, gum, gummies, jelly beans, nougats, fondant cream, combinations of one or more of the foregoing, and edible flavor compositions incorporating one or more of the foregoing.

Exemplary baked goods include, but are not limited to, sandwich biscuits (alfajors), bread, packaged/industrial bread, bulk/handmade bread, pastries, cakes, packaged/industrial cakes, bulk/handmade cakes, biscuits, chocolate-coated biscuits, sandwich biscuits, filled biscuits, flavored biscuits and crackers, bread substitutes.

Exemplary confectionary products include, but are not limited to, breakfast cereal flakes, ready-to-eat ("rte") cereal, family breakfast cereal flakes, breakfast foods, other ready-to-eat cereal, children's breakfast cereal flakes, hot cereal.

Exemplary flavored products include, but are not limited to, salty snacks (potato chips, crackers, nuts, fried tortillas, pretzels, cheese snacks, corn snacks, potato snacks, ready-to-eat popcorn, microwaveable popcorn, pork rinds, nuts, crackers, crisp snacks, breakfast cereal chips, meats, aspics, marinated meats (ham, salted pork), lunch/breakfast meats (hot dogs, cold-eaten sliced meats, sausages), tomato products, margarine, peanut butter, soups (light soup, canned soup, cream, ready-to-eat soup, UHT), canned vegetables, pasta sauce.

Exemplary dairy products include, but are not limited to, cheese condiment, cheese-based product, ice cream, consumable ice cream, single serving ice cream, multi-pack milk ice cream, multi-pack water ice cream, returning home milk ice cream, ice cream dessert, bulk ice cream, returning home water ice cream, frozen yogurt, handmade ice cream, dairy product, fresh/pasteurized milk, whole fresh/pasteurized milk, semi-skimmed fresh/pasteurized milk, longer/ultra-warm milk with whole milk shelf life, longer/ultra-warm milk with semi-skimmed milk, longer/ultra-warm milk with non-fat shelf life, goat milk, condensed/dehydrated milk, purified condensed/dehydrated milk, Flavored, functional and other condensed milks, flavored milk drinks, flavored milk drink only dairy products, flavored milk drinks with fruit juice, soy milk, yogurt drinks, fermented milk drinks, coffee whiteners, milk powders, flavored milk drinks, creams, yogurts, pure/natural yogurts, flavored yogurts, fruit-added yogurts, probiotic yogurts, drinking yogurts, regular drinking yogurts, probiotic drinking yogurts, frozen and shelf-stable snacks, dairy-based snacks, soy-based snacks.

Exemplary beverages include, but are not limited to, flavored water, soft drinks, juice beverages, coffee-based beverages, tea-based beverages, juice-based beverages (including fruits and vegetables), milk-based beverages, jelly beverages, carbonated or non-carbonated beverages, powdered beverages, alcoholic or non-alcoholic beverages.

Exemplary fermented food products include, but are not limited to, cheese and cheese products, meat and meat products, soy and soy products, fish and fish products, grain and grain products, fruits and fruit products.

The compound of formula (I) may improve any aspect of the temporal profile of the taste and/or mouthfeel of the edible composition when added to the flavour composition and/or edible composition.

The compounds of formula (I) or flavour compositions comprising them may be incorporated into edible products in a wide range of carrying amounts. The amount depends on the nature and desired effect of the edible composition to be flavored and on the nature of the ingredients present in the composition. To obtain significant benefits attributed to the presence of the compound of formula (I), the flavour composition should be used in an amount such that the compound of formula (I) is present in an amount of 1 part per billion to 10 parts per million based on the total weight of the edible composition. Although amounts above it may be used, the beneficial effect is clearly rather low and undesirable off-flavours may become progressively apparent.

Significant sensory effects, such as salt, alcohol or cooling enhancement effects, can be achieved in edible products comprising salt or alcohol or cooling compounds when the compound of formula (I) is used at levels of 1-100 ppb.

When the compound of formula (I) is used at a level of 100-250ppb, meaningful sensory effects, such as umami taste enhancing effects, can be achieved in the edible product comprising the umami taste enhancer.

When the compound of formula (I) is used at a level of 250-500ppb, a meaningful organoleptic effect, in particular a mouthfeel-enhancing effect, can be achieved in the edible product.

When the compound of formula (I) is used at a level of 500-1000ppb, meaningful sensory effects, such as fat-enhancing effects, can be achieved in edible products comprising fat.

It is particularly advantageous to incorporate the compounds of formula (I) into edible products which are formed under high temperature conditions, such as baking, frying or processed by heat treatment, such as pasteurization or UHT conditions. At high preparation or processing temperatures, volatile flavour ingredients may be lost or degraded, with the result that the flavour intensity may be reduced and the basic and authentic flavour profile may be reduced. Such edible products include dairy products, snack foods, baked goods, powdered soft drinks and similar dry mixes and the like, fats and condiments, mayonnaise, dressings, soups and broths and beverages.

One particularly preferred type of edible composition of the present invention is powdered soft drinks and similar dry mix applications. Dry mix applications are well known in the art and include products in powder form that are intended to be reconstituted prior to consumption. They include powdered soups, powdered cake mixes, powdered chocolate drinks, instant coffee, condiments, fonds, and the like.

Dry powders formed by dispersion evaporation methods such as spray drying represent a very convenient vehicle for delivering aroma of an aroma oil quality to edible products.

Another particularly preferred category of edible compositions of the invention are snack foods. Snack foods are a well known type of product to those of ordinary skill in the food industry. These products are described above and include, but are not limited to, pretzels, corn chips, potato chips, puffed products, extruded products, tortilla chips, and the like. More particularly, the present invention relates to low fat snack food compositions. The low fat snack food composition comprises less than 30% by weight fat, more particularly 5-25% by weight fat.

A problem with fat reduction in snack food compositions is lack of taste and texture. Fat plays an important role in the way that the behavior of the raw dough during processing and significantly affects the quality, flavour and texture of the instant food. When the fat content in snack products is reduced or replaced by other ingredients (e.g. non-digestible fats, proteins, fibres, gums), the negative sensory effects (e.g. oral smearing, dryness, lack of crispness and lack of flavour) increase. Adverse sensory effects lead to a decrease in the palatability of the product.

Considerable effort has been expended in designing flavour compositions to overcome the problems associated with low fat snack foods. The flavors can be applied to the snack food as a topical coating in dry powder and/or liquid form (e.g., oil-based, water-based). Another method consists in adding spices to the dough.

Despite these various approaches to improving consumer appeal and palatability of snack foods, and in particular low fat snack foods, there remains a need for improved low fat snack foods having a coating thereon of the visual appeal, flavor and texture of full fat snack foods.

The compounds of formula (I) or flavour compositions comprising them may be incorporated into snack foods to impart an effective flavour and a mouthfeel with a pronounced rounded and plump feel. Furthermore, the taste and mouthfeel effect can be achieved even in low fat snack foods.

Accordingly, the present invention provides in another of its aspects a snack food comprising a flavour composition as described above. In a particular embodiment of the invention, the snack food has a fat content of about 40% by weight or less, more particularly about 30% by weight or less, still more particularly about 25% by weight or less, more particularly about 10% by weight or less, still more particularly about 5% by weight or less, still more particularly about 3% by weight or less of the total weight of the snack food.

Examples of snack foods are described above and include products processed by oven baking, extrusion or frying and processed from potatoes and/or corn and/or different grains such as rice or wheat.

Another particularly preferred type of edible composition of the invention is an alcoholic beverage.

The applicant has surprisingly found that the compound of formula (I) incorporated into an alcoholic beverage has the effect of increasing the alcoholic impact of the beverage.

Accordingly, the present invention provides, in another of its aspects, an alcoholic beverage comprising a compound of formula (I).

In another aspect of the invention there is provided a method of producing an enhanced alcoholic impact in an alcoholic beverage by incorporating into said beverage a compound of formula (I).

The compound of formula (I) may be incorporated into the alcoholic beverage in an amount of 1ppb to 1 ppm.

Another class of edible products is products in the form of tablets, capsules, powders, multiparticulates, etc. for oral ingestion. Such compounds may include pharmaceutical or nutraceutical dosage forms.

One group suffers from difficulties in swallowing tablets or capsules, powders, multiparticulates, etc. This problem is particularly pronounced in some consumer types, such as children and very old elderly or infirm persons. The applicant has surprisingly found that the compounds of formula (I) produce a significant salivation effect when ingested into the oral cavity. The incorporation of the compounds into these forms, particularly as part of a coating around the dosage form, may facilitate the swallowing process for consumers, particularly children and the elderly or infirm.

Accordingly, the present invention provides, in another of its aspects, an orally administrable dosage form, in particular in the form of a tablet, capsule, powder or multiparticulate, comprising a compound of formula (I).

Another preferred type of edible composition is a baked product. The compound of formula (I) may be incorporated topically or in the dough. Incorporation of the compound of formula (I) at levels of 1ppb to 1ppm makes the baked products less dry and more juicy.

Other preferred types of edible products are caloric or non-caloric beverages, which contain carbohydrate sweeteners, such as sucrose, high fructose corn syrup, fructose, and glucose; or high intensity non-nutritive sweeteners such as aspartame, acesulfame potassium, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside a, and/or other stevia-based sweeteners; and other optional ingredients such as fruit juices, organic acids such as citric acid, alcohols and functional ingredients.

Incorporation of a compound of formula (I) at a level of from 1ppb to 10ppm imparts an equal sweetness and a mouthfeel suggestive of sugar to said beverage comprising a sweetener at a level of less than 1% and up to about 20%.

Other preferred edible products are flavour compositions, in particular those based on soy or fish.

Incorporation of soy-based compositions (e.g. soy sauce) or fish meat-based compositions (e.g. fish dressing) containing 5-40% salt at levels of 1ppb to 10ppm was found to show lingering and rich strong umami taste.

Another preferred edible composition is a cloudy beverage composition.

Some beverages, such as juices, have a relatively high turbidity and thus an opaque appearance. It is generally desirable for beverages to have a relatively high turbidity, which may be desirable to provide a natural appearance to beverages with low juice content, or may be the cause associated with masking sedimentation or "crisping" in which flavor or pigment oils rise to the container surface during storage. Cloudy beverages are typically formed with the aid of a clouding agent. The clouding agent is typically provided in the form of an emulsion, or the clouding agent may be an integral part of the powdered beverage, which upon reconstitution, forms an emulsion, thereby providing a persistent clouding to the beverage.

The compounds of formula (I) can impart stability to clouding agents and beverage compositions containing them in addition to their distinctive organoleptic characteristics.

Other preferred edible products are those compositions formed by a ripening process. During food processing, the need frequently arises for food products to be maintained under well-defined conditions for extended periods of time in order to obtain food products of essential and well-recognized quality. A common term used for this process is ripening. Ripening is well known in some types of cheese, meat, soy sauce and wine, as well as in beer sausage, sauerkraut, tempeh and tofu processing. There are also specific steps that are carried out for specific reasons (for example removal of water or removal of off-flavours) which have a beneficial effect on the food product. Examples thereof are conched chocolate and dried noodles, vegetables and fruits. The conversion to improve the quality of the food is induced by chemical conversion, enzymatic conversion or fermentative conversion. All of these transformations are slow and thus expensive; they are also not entirely predictable or controllable.

The compounds of formula (I) have significant properties in terms of their true taste profile for addition to edible products into which they are incorporated, and may be added to edible products during cooking in order to reduce storage time without adversely affecting the taste quality of the cooked product.

Accordingly, the present invention provides in another aspect a method of ripening a product selected from the group consisting of cheese, meat, soy sauce and wine, beer, sausage, sauerkraut, tempeh and tofu, comprising the step of ripening the product in the presence of a compound of formula (I).

In another aspect the invention provides a method of conching chocolate comprising the step of adding to the chocolate a compound of formula (I) or a flavour composition comprising same.

The invention will now be further described with reference to the following non-limiting examples. These embodiments are for illustrative purposes only, and it is to be understood that changes and modifications may be made by those skilled in the art.

Example 1: 4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester

In a 250mL round bottom flask equipped with a stirrer, cooler and dropping funnel, methyl 2-amino-4-methylpentanoate, HCl (3g, 16.51mmol) was dissolved in dichloromethane (DCM; 100 mL). Triethylamine (1.519g, 15.01mmol) was added at-15 ℃. While stirring, linoleic acid (4.21g, 15.01mmol) was added.

A solution of N, N-dicyclohexylcarbodiimide (DCC; 3.10g, 15.01mmol) in 10mL DCM was added dropwise at 0 ℃. The reaction mixture was stirred at 0 ℃ for 1 hour and at room temperature for 3 hours.

The dicyclohexylurea formed was removed by filtration from the reaction mixture.

The filtrate was washed with saturated sodium bicarbonate solution, dilute hydrochloric acid solution and water. The organic layer was separated, dried and evaporated to give 3g of oil. The oil was purified by flash column chromatography eluting with DCM/methanol to give methyl 4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoate with a purity of 95% yield: 31 percent.

¹H NMR (600MHz, chloroform-d) ppm 0.87-0.92(t, J ═ 6.82Hz, 3H, H-C (18))0.93-0.97(m, 6H, H-C (23, 24))1.26-1.46(m, 14H, H-C (4, 5, 6, 7, 15, 16, 17)1.45-1.70(m, 5H, H-C (3, 21, 22))2.13(m, 4H, H-C (8, 14))2.13-2.33(m, 2H, H-C (2))2.69-2.88(m, 2H, H-C (11))3.70-3.90(s, 3H, H-C (25))4.62-4.74(m, 1H, H-C (20))5.30-5.49(m, 4H, 9, 10H (9, 10H-C (26, 26 Hz)).

¹³C NMR (151MHz, chloroform-d) ppm 14.08(C (18)), 21.95(C (24)), 22.77C (23)), 24.85C (22))25.53C (3)), 25.58C (11))27.10-27.31(C (8, 14)), 29.02-29.69C (4, 5, 6, 7, 15))31.48C (16)), 36.54C (2)), 41.76C (21)), 41.76C (21)), 50.47C (20)), 52.22C (25)), 127.79-128.08C (9, 10, 12, 13), 1.76C (21)), and72.83C(19)，173.75C(1))。

example 2: (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate

According to the same procedure as in example 1, (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate was prepared from leucine methyl ester and geranic acid in a yield of 13%.

¹H NMR(600MHz，DMSO-d₆)δppm 0.67-0.93(m，6H)1.37-1.74(m，10H)1.93-2.17(m，6H)2.41-2.65(m，1H)3.50-3.66(m，3H)4.25(ddd，J＝10.05，7.13，5.15Hz，1H)4.96-5.14(m，1H)5.60-5.75(m，1H)7.95-8.15(m，1H)。

¹³C NMR(151MHz，DMSO-d₆)δppm 17.46(s，1C)17.51(s，1C)17.74(s，1C)21.22(s，1C)22.73(s，1C)24.27(s，1C)24.29(s，1C)24.56(s，1C)25.43(s，1C)25.45(s，1C)25.65(s，1C)26.34(s，1C)32.20(s，1C)(s，1C)39.64(s，1C)39.79(s，1C)39.92(s，1C)40.19(s，1C)49.89(s，1C)49.95(s，1C)51.67(s，1C)51.69(s，1C)117.91(s，1C)123.40(s，1C)124.02(s，1C)131.40(s，1C)152.82(s，1C)166.06(s，1C)173.34(s，1C)。

Example 3: (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate

According to the same procedure as in example 1, (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate was prepared from alanine methyl ester and geranic acid in a yield of 13%.

¹H NMR(600MHz，DMSO-d₆)δppm 1.12-1.27(m，6H)1.45-1.66(m，12H)1.76(d，J＝1.37Hz，2H)1.88-2.14(m，9H)2.47(s，1H)4.09-4.29(m，1H)4.96-5.15(m，1H)5.59-5.72(m，1H)8.13(d，J＝6.87Hz，1H)。

¹³C NMR(151MHz，DMSO-d₆)δppm 16.95(s，1C)17.49(s，1C)17.53(s，1C)17.72(s，1C)24.60(s，1C)25.46(s，1C)25.65(s，1C)26.38(s，1C)32.25(s，1C)40.18(s，1C)47.24(s，1C)47.27(s，1C)51.71(s，1C)51.73(s，1C)117.90(s，1C)118.66(s，1C)123.39(s，1C)124.06(s，1C)131.41(s，1C)152.86(s，1C)165.80(s，1C)173.41(s，1C)。

Example 4: (E) -1- (3, 7-Dimethyloctyl-2, 6-dienoyl) pyrrolidine-2-carboxylic acid methyl ester

According to the same procedure as in example 1, (E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate was prepared from methyl proline and geranic acid in a yield of 65%.

¹H NMR(600MHz，DMSO-d₆)δppm 1.43-1.58(m，3H)1.58-1.67(m，3H)1.69-1.97(m，6H)1.97-2.19(m，4H)3.12-3.38(m，2H)3.38-3.52(m，2H)3.52-3.71(m，3H)4.26(dd，J＝8.59，4.47Hz，1H)4.47-4.59(m，1H)4.98-5.13(m，1H)5.61(s，1H)5.72(d，J＝0.69Hz，1H)5.79-5.91(m，1H)。

¹³C NMR(151MHz，DMSO-d₆)δppm 17.51(s，1C)17.59(s，1C)18.02(s，1C)24.50(s，1C)25.44(s，1C)25.47(s，1C)25.65(s，1C)28.75(s，1C)46.85(s，1C)51.66(s，1C)58.07(s，1C)117.17(s，1C)123.52(s，1C)131.37(s，1C)165.14(s，1C)172.67(s，1C)。

Example 5: (E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -3- (1H-imidazol-4-yl) propionate

According to the same procedure as in example 1, methyl (E) -2- (3, 7-dimethylocta-2, 6-dienamido) -3- (1H-imidazol-4-yl) propionate was prepared from histidine methyl ester and geranic acid in a yield of 13%.

¹H NMR(600MHz，DMSO-d₆)δppm 1.45-1.67(m，6H)1.92-2.13(m，6H)2.47(s，2H)2.82(d，J＝12.37Hz，2H)3.55(s，2H)4.34-4.48(m，1H)4.94-5.08(m，1H)5.53-5.71(m，1H)6.50-6.89(m，1H)7.49(br.s.，1H)7.96-8.22(m，1H)11.70-11.87(m，1H)。

¹³C NMR(151MHz，DMSO-d₆)δppm 18.04(s，1C)18.08(s，1C)18.27(s，1C)24.05(s，1C)25.11(s，1C)25.95(s，1C)25.99(s，1C)26.02(s，1C)26.05(s，1C)26.17(s，1C)26.89(s，1C)27.18(s，1C)31.22(s，1C)32.79(s，1C)40.58(s，1C)40.69(s，1C)52.24(s，1C)52.80(s，1C)118.51(s，1C)123.94(s，1C)124.57(s，1C)131.96(s，1C)135.41(s，1C)166.48(s，1C)207.02(s，1C)。

Example 6: methyl 1- ((9Z,12Z) -octadeca-9, 12-dienoyl) pyrrolidine-2-carboxylate (methyl N-linoleoyl proline)

According to the same procedure as in example 1, methyl 1- ((9Z,12Z) -octadeca-9, 12-dienoyl) pyrrolidine-2-carboxylate was prepared from proline methyl ester and linoleic acid in a yield of 25%.

¹H NMR (600MHz, chloroform-d) δ ppm 0.86-0.93(t, J ═ 6.87, 3H, H-C (18))1.24-1.40(m, 14H, H-C (4, 5, 6, 7, 15, 16, 17))1.63-1.71(m, 2H, H-C (3))1.95-2.02(m, 2H, H-C (22)2.02-2.12(m, 5H, H-C (8, 14, 21)2.12-2.22(m, 1H, H-C (21))2.23-2.38(m, 2H, H-C2)))4.49 (m, 2H, J ═ 8.59, 3.78Hz, 1H, H-C20))5.22-5.49(m, 4H, H-C (9, 10, 12, 13).

¹³C NMR (151MHz, chloroform-d) delta ppm 14.07(C (18))22.57(C (17))24.57(C (3))24.82(C (22))25.61(C (11))27.15-27.27(C (8, 14)29.07-29.72(C (4, 5, 6, 7, 15, 21)) (C)31.51(C (16))34.47(C (2))46.97(C (23))52.15(C (24))58.54(C (20))127.84-128.03(C (10, 12))130.03-130.25(C (9, 13))172.08(C (1, 19)).

Example 7: methyl 2- ((9Z,12Z,15Z) -octadeca-9, 12, 15-trienylamido) propanoate (methyl N-linolenoylalanine)

Methyl 2- ((9Z,12Z,15Z) -octadeca-9, 12, 15-trienoylamino) propionate was prepared from methyl alanine and linolenic acid according to the same procedure as in example 1 in a yield of 25%.

¹H NMR(600MHz，DMSO-d₆)δppm 0.92(t，J＝7.39Hz，3H)1.14-1.19(m，1H)1.17-1.39(m，20H)1.39-1.59(m，3H)1.92-2.13(m，9H)2.62-2.84(m，5H)3.60(s，4H)4.23(t，J＝7.22Hz，1H)5.22-5.40(m，7H)8.20(d，J＝6.87Hz，1H)。

¹³C NMR(151MHz，DMSO-d₆)δppm 14.43(s，1C)14.62(s，1C)17.46(s，1C)20.56(s，1C)22.51(s，1C)25.63(s，1C)25.67(s，1C)25.72(s，1C)27.13(s，1C)27.17(s，1C)29.08(s，1C)29.11(s，1C)29.21(s，1C)29.26(s，1C)29.55(s，1C)31.43(s，1C)35.40(s，1C)47.93(s，1C)52.23(s，1C)127.48(s，1C)128.06(s，1C)128.26(s，1C)128.42(s，1C)128.45(s，1C)130.24(s，1C)130.41(s，1C)132.00(s，1C)172.63(s，1C)173.79(s，1C)。

Example 8: mango flavored beverage

Mango flavored beverages were prepared using standard mango essence (0.05% w/w), mango juice (0.18% w/w), sugar (8% w/w) and citric acid (0.1% w/w). The beverage was evaluated by a panel of experienced tasters.

a) When 0.5ppm methyl N-linoleoyl proline (example 6) was administered to a mango beverage, the panel agreed that this beverage tasted more fruity and peach-like than the reference beverage.

b) When 0.5ppm methyl N-linolenoyl alanine (example 7) was administered to a mango drink, the panel agreed that this drink tasted more plump, more fat-like feeling than the reference drink.

Claims

1. Flavour composition comprising a flavour co-ingredient and a compound of formula (I),

wherein:

R⁵is C₁-C₃Alkyl radical, and

a) when n is 1;

i)R³and R⁴Is hydrogen, and R²Is a residue of a proteinogenic amino acid; or

ii)R²And R³Is methyl, and R⁴Is hydrogen; or R⁴Is hydrogen, and R²And R³Together with the carbon atom to which they are attached form a cyclopropyl group; or

iii)R²Is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-; or

b) When n is 2 or 3, R²、R³And R⁴Is hydrogen, and

wherein the compound of formula (I) is selected from:

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate;

(E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -3- (1H-imidazol-4-yl) propionate;

1- ((9Z,12Z) -octadeca-9, 12-dienoyl) pyrrolidine-2-carboxylic acid methyl ester; and

4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester.

2. A flavour composition according to claim 1 wherein the flavour co-ingredient is selected from: sugars, fats, sodium chloride, monosodium glutamate, calcium ions, phosphate ions, organic acids, proteins, purines, flavors, and mixtures thereof.

3. An edible product comprising a compound of formula (I),

wherein:

R⁵is C₁-C₃Alkyl radical, and

a) when n is 1;

i)R³and R⁴Is hydrogen, and R²Is a residue of a proteinogenic amino acid; or

iii)R²Is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-; or

b) When n is 2 or 3, R²、R³And R⁴Is hydrogen, and

wherein the compound of formula (I) is selected from:

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate;

(E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate;

4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester.

4. A method of modifying the taste of an edible composition comprising at least one flavour co-ingredient, said method comprising the step of adding to the edible composition a compound of formula (I),

wherein:

R⁵is C₁-C₃Alkyl radical, and

a) when n is 1;

i)R³and R⁴Is hydrogen, and R²Is a residue of a proteinogenic amino acid; or

iii)R²Is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-; or

b) When n is2 or 3, R²、R³And R⁴Is hydrogen, and

wherein the compound of formula (I) is selected from:

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate;

(E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate;

4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester.

5. Use of a compound of formula (I) as a taste modifier in a consumer product,

wherein:

R⁵is C₁-C₃Alkyl radical, and

a) when n is 1;

i)R³and R⁴Is hydrogen, and R²Is a residue of a proteinogenic amino acid; or

iii)R²Is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-; or

b) When n is 2 or 3, R²、R³And R⁴Is hydrogen, and

wherein the compound of formula (I) is selected from:

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate;

(E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate;

4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester.

6. Taste modifiers in consumer products, comprising compounds of formula (I),

wherein:

R⁵is C₁-C₃Alkyl radical, and

a) when n is 1;

i)R³and R⁴Is hydrogen, and R²Is a residue of a proteinogenic amino acid; or

iii)R²Is hydrogen, and R³And R⁴Together are-CH₂-CH₂-CH₂-; or

b) When n is 2 or 3, R²、R³And R⁴Is hydrogen, and

wherein the compound of formula (I) is selected from:

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) -4-methylpentanoate;

(E) -methyl 2- (3, 7-dimethylocta-2, 6-dienamido) propionate;

(E) -methyl 1- (3, 7-dimethylocta-2, 6-dienoyl) pyrrolidine-2-carboxylate;

4-methyl-2- ((9Z,12Z) -octadeca-9, 12-dienamido) pentanoic acid methyl ester.